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[ CAS No. 180181-02-6 ] {[proInfo.proName]}

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Chemical Structure| 180181-02-6
Chemical Structure| 180181-02-6
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Product Details of [ 180181-02-6 ]

CAS No. :180181-02-6 MDL No. :MFCD09952625
Formula : C10H19NO4 Boiling Point : No data available
Linear Structure Formula :- InChI Key :LSZXQEWVQORQBO-UHFFFAOYSA-N
M.W : 217.26 Pubchem ID :11790631
Synonyms :
Chemical Name :3-(Boc-amino)-2,2-dimethylpropionic Acid

Safety of [ 180181-02-6 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 180181-02-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 180181-02-6 ]

[ 180181-02-6 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 162465-33-0 ]
  • [ 180181-02-6 ]
  • [ 186193-09-9 ]
  • 2
  • (S)-2-Amino-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-2-(3-chloro-4-methoxy-phenyl)-1-(2,2,2-trichloro-ethoxycarbonyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester; compound with trifluoro-acetic acid [ No CAS ]
  • [ 180181-02-6 ]
  • [ 211678-37-4 ]
  • 3
  • [ 180181-02-6 ]
  • 3-amino-2,2-dimethyl-propionic acid methyl ester; compound with trifluoro-acetic acid [ No CAS ]
  • methyl 3-<(3-(<(tert-butoxy)carbonyl>amino)-2,2-dimethylpropanoyl)amino>-2,2-dimethylpropanoate [ No CAS ]
  • 4
  • [ 180181-02-6 ]
  • 3-(3-amino-2,2-dimethyl-propionylamino)-2,2-dimethyl-propionic acid methyl ester; compound with trifluoro-acetic acid [ No CAS ]
  • [ 220145-06-2 ]
  • 6
  • [ 204514-14-7 ]
  • [ 180181-02-6 ]
  • 7
  • [ 180181-02-6 ]
  • 3-[3-(3-amino-2,2-dimethyl-propionylamino)-2,2-dimethyl-propionylamino]-2,2-dimethyl-propionic acid methyl ester; compound with trifluoro-acetic acid [ No CAS ]
  • [ 220145-16-4 ]
  • 8
  • [ 180181-02-6 ]
  • C5(13)CH13NO2*C2HF3O2 [ No CAS ]
  • C15(13)CH30N2O5 [ No CAS ]
  • 9
  • [ 180181-02-6 ]
  • C14(13)C2H31N2(15)NO4*C2HF3O2 [ No CAS ]
  • C24(13)C2H48N3(15)NO7 [ No CAS ]
  • 10
  • [ 180181-02-6 ]
  • [ 204397-94-4 ]
  • [ 204397-95-5 ]
YieldReaction ConditionsOperation in experiment
75% A solution of fragment C' acid (0.040 g, 0.184 mmole) and carbonyldiimidazole (CDI) (0.040 g, 0.25 mmole) in 2 mL of toluene was heated under nitrogen at 45 C. for 45 minutes. [00475] Following the addition of the alcohol (shown above) (0.10 g, 0.15 mmole) in 1 mL of toluene, the reaction was again heated at 45 C. for 4 hrs. Upon cooling to room temperature, the reaction mixture was diluted with EtOAc (100 mL), washed with 0.1 N HCl (1×10 mL), water (1×10 mL), saturated NaHCO3 (1×10 mL) and brine (1×10 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo to provide the crude ester as a yellow foam. Purification by radial PLC (silica gel, 50% EtOAc/hexanes) provided the pure ester (0.097) g in 75% yield as a yellow solid: [alpha]20D +17.2 (c 0.58, CHCl3); 1H NMR (300 MHz, CDCl3) delta 7.40-7.34 (d, 2H, J=8.5 Hz), 7.29-7.22 (m, 3H), 7.13-7.00 (m, 3H), 6.92-6.86 (d, 1H, J=8.8 Hz), 6.86-6.76 (m, 1H), 6.50-6.38 (d, 1H, J=15.9 Hz), 6.10-5.97 (dd, 1H, J=15.8, 8.8 Hz), 5.85-5.75 (d, 1H, J=15.1 Hz), 5.55-5.45 (d, 1H, J=7.9 Hz), 5.15-5.06 (m, 1H), 5.06-4.96 (m, 1H), 4.95-4.85 (m, 1H), 4.83-4.72 (dd, 1H, J=10.0, 3.0 Hz), 3.92 (s, 3H), 3.53-3.35 (m, 3H), 3.22-3.06 (m, 3H), 2.65-2.50 (m, 2H), 2.48-2.35 (m, 1H), 1.80-1.65 (m, 2H), 1.49 (s, 9H), 1.40 (s, 6H), 1.27 (s, 3H), 1.21 (s, 3H), 1.20-1.15 (d, 3H, J=6.9 Hz), 0.86-0.77 (d, 6H, J=6.3 Hz); 13C NMR (63 MHz, CDCl3) delta 177.8, 170.5, 170.4 165.1, 156.0, 153.9, 150.0, 142.0, 134.5, 130.8, 130.6, 130.4, 129.6, 128.2, 126.9, 124.6, 122.4, 121.5, 112.2, 79.2, 71.3, 56.0, 54.4, 48.2, 46.4, 44.0, 42.7, 42.1, 39.5, 36.5, 35.2, 28.3, 24.9, 24.5, 22.9, 22.8, 22.7, 21.3, 17.2; IR (CHCl3) 3425, 2970, 2934, 2874, 1746, 1711, 1684, 1604, 1505, 1442, 1394, 1368, 1305, 1258, 1166, 1123, 1067, 1015, 971 cm-1; Anal. (C41H55ClN3O9) C, H, N.
  • 11
  • [ 180181-02-6 ]
  • [ 204397-82-0 ]
  • [ 204397-80-8 ]
YieldReaction ConditionsOperation in experiment
85% A mixture of the free acid of fragment C' (0.22 g, 1.02 mmol), DMAP (0.032 g, 0.26 mmol) and DCC (0.21 g, 1.02 mmol) was stirred for 30 min at 0 C. in 6.5 mL of CH2Cl2. The free alcohol 29 (0.35 g, 0.51 mmol) in 6.0 mL of CH2Cl2 was added dropwise. The mixture was stirred at 0 C. for 10 min and at room temperature for 24 h and finally was heated at reflux for 3 h and cooled back to room temperature. The reaction mixture was concentrated in vacuo and filtered through Celite using EtOAc. The resulting residue was purified using column chromatography (silica gel, 60-70% EtOAc/hexanes) to give 0.38 g (85%) of the ester above as a white solid: [alpha]20D +23.2 (c 1.0, CHCl3); 1H NMR (300 MHz, CDCl3) delta 7.4-7.2 (m, 6H), 7.12-7.08 (dd, 1H, J=8.4, 2.0 Hz), 6.9-6.87 (d, 1H, J=8.5 Hz), 6.87-6.75 (m, 1H), 6.47-6.42 (d, 1H, J=15.8 Hz), 6.11-6.03 (dd, 1H, J=15.8, 8.8 Hz), 5.82-5.77 (d, 1H, J=14.9 Hz), 5.61-5.58 (d, 1H, J=7.8 Hz), 5.12 (s, 2H), 5.12-4.75 (m, 4H), 3.9 (s, 3H), 3.49-3.42 (dd, 1H, J=13.4, 8.7 Hz), 3.29-3.27 (d, 1H, J=6.5 Hz), 3.2-3.1 (m, 3H), 2.65-2.3 (m, 3H), 1.8-1.6 (m, 3H), 1.47 (s, 9H), 1.45-1.3 (m, 1H), 1.3-1.15 (m, 15H), 0.79-0.75 (t, 6H, J=6.4 Hz); 13C NMR (75 MHz, CDCl3) delta 177.8, 170.4, 165.1, 153.9, 141.9, 136.7, 135.1, 131.1, 130.8, 129.7, 128.3, 128.2, 126.2, 124.6, 122.4, 112.2, 76.9, 71.3, 66.0, 56.0, 54.4, 48.2, 46.4, 43.7, 42.6, 42.2, 39.4, 36.4, 35.2, 28.3, 24.5, 22.8, 22.6, 21.2, 17.2; IR (CHCl3) 3426, 2968, 2935, 2874, 2841, 1746, 1713, 1684, 1652, 1504, 1486, 1474, 1368, 1318, 1304, 1259, 1244, 1165, 1151, 1067 cm-1; FAB HRMS [M-BOC+H] calcd for (C42H57ClN3O9) 782.3783, found 782.3788.
  • 12
  • [ 180181-02-6 ]
  • [ 312639-10-4 ]
  • {2-[1-(4-chloro-benzyl)-2-(4-cyclohexyl-4-[1,2,4]triazol-1-ylmethyl-piperidin-1-yl)-2-oxo-ethylcarbamoyl]-2-methyl-propyl}-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
  • 14
  • [ 180181-02-6 ]
  • [ 50-89-5 ]
  • BocNH-HE-T [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In chloroform; N,N-dimethyl-formamide; at 0 - 20℃; for 20h; 4-Boc-amino-2,2-dimethybutyric acid (compound 16, 0.50 g, 2.16 mmol) was dissolved in a mixture of chloroform (10 mL) and DMF (5 mL), and thymidine (compound 17, 0.79 g, 3.25 mmol) was added. The reaction mixture was cooled in an ice bath, and EDC (0.62 g, 3.25 mmol) was added, followed by DMAP (0.4Og, 3.25 mmol). The reaction mixture was allowed to warm to room temperature for 20 hours with stirring. Solvent was removed in <n="52"/>7 078597vacuo and the residue was suspended in ethyl acetate, washed with 0.1N HCl, and brine. Organic layer was dried over anhydrous sodium sulfate and the solvent was removed in vacuo to give a crude oil. Flash column chromatography on silica gel using DCM / EtOAc (40:60, v/v) gave 0.28 g of the desired product: 13C NMR d 177.21, 164.08, 156.41, 150.80, 135.46, 111.49, 85.43, 84.30, 80.21, 71.28, 63.77, 41.67, 41.08, 40.00, 37.69, 36.99, 28.87, 26.14, 25.55, 13.06.
  • 15
  • [ 19036-43-2 ]
  • [ 24424-99-5 ]
  • [ 180181-02-6 ]
YieldReaction ConditionsOperation in experiment
91% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 60℃; for 16h; Example 6: Synthesis of 3-(tert-butoxycarbonylamino)-2,2-dimethylpropanoic acid (19)[00156] 3-Amino-2,2-dimethylpropanoic acid (18) (1.2 g, 10.2 mmol), Boc anhydride (2.3 g, 10.2 mmol) and DIPEA (1.85 mL, 10.23 mmol) were stirred under argon in DMF (30 mL) at 60 C for 16 h. The reaction was concentrated in vacuo, taken up in EtOAc, washed with saturated NH4C1 solution, and concentrated in vacuo to give 3-(teri-butoxycarbonylamino)-2,2-dimethylpropanoic acid (19) (2.0 g, 91 %); 1H NMR (300 mHz - CDCl3) 6 1.33 (s, 6 H), 1.37 (s, 9 H), 2.69 (s, 2 H).
63% With sodium hydroxide; In water; tert-butyl alcohol; at 20℃; for 16h; Preparational Example 21 Preparation of 3-(t-butoxycarbonylamino)-2,2-dimethylpropanoic acid 256 mg (2.22 mmol) of the -amino-2,2-dimethylpropanoic acid prepared in Preparational Example 20 was dissolved in 2.0 ml of water and 3.0 ml of t-BuOH, to which 4.0 ml of 1.0 N NaOH solution and 725 mg (3.32 mmol) of Boc2O were added. The mixture was stirred at room temperature for 16 hours, followed by evaporation under reduced pressure to eliminate the solvent. The residue was acidized with 1 N HCl to be pH 3, followed by extraction with 320 ml of ethyl acetate. The extract was dried over anhydrous magnesium sulfate, followed by evaporation under reduced pressure to give 305 mg of 3-(t-butoxycarbonylamino)-2,2-dimethylpropanoic acid (yield: 63%). 1H NMR (400 MHz, CDCl3) delta 3.25 (s, 2H), 1.44 (s, 9H), 1.18 (s, 6H)
63% With sodium hydroxide; In water; tert-butyl alcohol; at 20℃; for 16h; 256 mg (2.22 mmol) of the -amino-2,2-dimethylpropanoic acid prepared in Preparational Example 20 was dissolved in 2.0 ml of water and 3.0 ml of t-BuOH, to which 4.0 ml of 1.0 N NaOH solution and 725 mg (3.32 mmol) of Boc2O were added. The mixture was stirred at room temperature for 16 hours, followed by evaporation under reduced pressure to eliminate the solvent. The residue was acidized with 1 N HCl to be pH 3, followed by extraction with 320 ml of ethyl acetate. The extract was dried over anhydrous magnesium sulfate, followed by evaporation under reduced pressure to give 305 mg of 3-(t-butoxycarbonylamino)-2,2-dimethylpropanoic acid (yield: 63%). 1H NMR (400 MHz, CDCl3) delta 3.25 (s, 2H), 1.44 (s, 9H), 1.18 (s, 6H)
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